CH423036A - Process for the production of azo dyes that are sparingly soluble in water - Google Patents
Process for the production of azo dyes that are sparingly soluble in waterInfo
- Publication number
- CH423036A CH423036A CH807560A CH807560A CH423036A CH 423036 A CH423036 A CH 423036A CH 807560 A CH807560 A CH 807560A CH 807560 A CH807560 A CH 807560A CH 423036 A CH423036 A CH 423036A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- red
- alkyl
- hydrogen
- water
- Prior art date
Links
- 239000000987 azo dye Substances 0.000 title claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- -1 ethylphenyl Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 11
- 239000000835 fiber Substances 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 125000006519 CCH3 Chemical group 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Verfahren zur Herstellung in Wasser schwer löslicher Azofarbstoffe Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung neuer, in Wasser schwer löslicher Azofarbstoffe der allgemeinen Formel
EMI0001.0008
worin X Stickstoff, C-H, C-Alkyl, C-CF3, C-Phenyl, C-(Methylphenyl), C-(Äthylphenyl), C-(Dime- t'hylphenyl)
oder C-(Halogenphenyl), Alkyl einen Alkylrest mit 1-4 Kohlenstoffatomen, M Wasserstoff, Hydroxyl!, einen Alkoxy-, einen gegebenenfalls substituierten Acetoxy oder einen Carbaminsäurealkylesterrest, R einen zweiwertigen aliphatischen Rest mit 1-4. Kohlenstoff atomen, s Wasserstoff oder Methyl,
t Wasserstoff oder eine Hyd'roxylgruppe und Y Wasserstoff, Halogen, einen niedrigmoleku- laren Alkyl- oder Alkoxy-, den Trifluormethyl-, den Trifluoracetyl- oder einen Alkanoylamino- rest mit höchstens 18 Kohlenstoffatomen bedeuten. Die neuen, in Wasser schwer löslichen Azofarb- stoffe ziehen zum Teil in Suspension auf synthetische Podyamidfasern, auf Celluloseesterfasern (z.
B. Acetat kunstseide, Triacetatkunstseide), Polyvinylfasern, Poly esterfasern in brillanten roten und violetten Tönen auf. Ihre Färbungen zeichnen sich durch vorzügliche Echtheitseigenschaften aus. Zum Teil sind die neuen Farbstoffe auch zum Färben von Kunststoffen, wor unter fösungsmittelfreie und lösungsmittelhaltige Mas sen aus Kunststoffen oder Kunstharzen verstanden werden, geeignet.
Das Verfahren zur Herstellung der in Wasser schwer löslichen Azofarbstoffe besteht darin, dass 1 Mol eines diazotierten Amins der Formel
EMI0001.0056
worin X die zuvor genannten Bedeutungen besitzt, mit 1 Mol einer Azokomponente der Formel
EMI0001.0059
worin M, R, s, t und Y die zuvor genannten Bedeu tungen besitzen, umsetzt.
Die Kupplung der Diazoverbindungen mit den Azokomponenten erfolgt vorzugsweise in saurem, ge gebenenfalls gepuffertem Medium. Wie die im Hauptpatent beschriebenen und her- gestellten neuen Azofarbstoffe, können auch die in der nachfolgenden Tabelle aufgeführten Farbstoffe in entsprechender Weise hergestellt werden.
Sie besit- zen gutes Ziehvermögen und zum Teil noch erhöhte Nuancenreinheit. Die Farbstoffe entsprechen der Formel
EMI0002.0014
EMI0002.0015
<I>Tabelle</I>
<tb> Beispiel <SEP> Nr.
<SEP> X <SEP> y <SEP> s <SEP> t <SEP> u <SEP> w <SEP> Farbton <SEP> auf <SEP> Acetat
<tb> 1 <SEP> C-H <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> rot
<tb> 2 <SEP> C-H <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH2-OH <SEP> rot
<tb> 3 <SEP> C-H <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH3 <SEP> rot
<tb> 4 <SEP> C-H <SEP> Cl <SEP> CH3 <SEP> H <SEP> H <SEP> OH <SEP> rot
<tb> 5 <SEP> C-H <SEP> Cl <SEP> CH3 <SEP> H <SEP> OH <SEP> <B>CH2--OH</B> <SEP> rot
<tb> 6 <SEP> <B>C <SEP> -H</B> <SEP> Cl <SEP> CH3 <SEP> H <SEP> OH <SEP> CH3 <SEP> rot
<tb> 7 <SEP> C-H <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> rotviolett
<tb> 8 <SEP> C-H <SEP> CHa <SEP> H <SEP> H <SEP> OH <SEP> <B>CH2--OH</B> <SEP> rotviolett
<tb> 9 <SEP> C-H <SEP> CH3 <SEP> H <SEP> H <SEP> OH <SEP> CH3 <SEP> rotviolett
<tb> 10 <SEP> GH <SEP> CH3 <SEP> H <SEP> OH <SEP> H <SEP> OH <SEP> rotviolett
<tb> 11 <SEP> C-H
<SEP> CH3 <SEP> H <SEP> OH <SEP> OH <SEP> CH2-OH <SEP> rotviolett
<tb> 12 <SEP> GH <SEP> CHs <SEP> H <SEP> OH <SEP> OH <SEP> CH3 <SEP> rotviolett
<tb> 13 <SEP> N <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> rot
<tb> 14 <SEP> N <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> <B>CH2--OH</B> <SEP> rot
<tb> 15 <SEP> N <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH3 <SEP> rot
<tb> 16 <SEP> CJCH3 <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> rot
<tb> 17 <SEP> C-CH3 <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH2-OH <SEP> rot
<tb> 18 <SEP> C-CH3 <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CHs <SEP> rot
<tb> 19 <SEP> C-H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> OH <SEP> rotviolett
<tb> 20 <SEP> C-H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OH <SEP> <B>CH2--OH</B> <SEP> rotviolett
<tb> 21 <SEP> C-H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OH <SEP> CH3 <SEP> rotviolett
<tb> 22 <SEP> C-CH3 <SEP> CH3 <SEP> CH3
<SEP> H <SEP> H <SEP> OH <SEP> rotviolett
<tb> 23 <SEP> C-CHS <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OH <SEP> CH2-OH <SEP> rotviolett
Process for the preparation of new azo dyes of the general formula which are sparingly soluble in water The present invention relates to a process for the preparation of new azo dyes of the general formula which are sparingly soluble in water
EMI0001.0008
where X is nitrogen, C-H, C-alkyl, C-CF3, C-phenyl, C- (methylphenyl), C- (ethylphenyl), C- (dimethylphenyl)
or C- (halophenyl), alkyl is an alkyl radical with 1-4 carbon atoms, M is hydrogen, hydroxyl !, an alkoxy, an optionally substituted acetoxy or an alkyl carbamic acid radical, R is a divalent aliphatic radical with 1-4. Carbon atoms, s hydrogen or methyl,
t denotes hydrogen or a hydroxyl group and Y denotes hydrogen, halogen, a low molecular weight alkyl or alkoxy, trifluoromethyl, trifluoroacetyl or alkanoylamino radical with at most 18 carbon atoms. Some of the new azo dyes, which are sparingly soluble in water, move in suspension onto synthetic podyamide fibers, onto cellulose ester fibers (e.
B. acetate rayon, triacetate rayon), polyvinyl fibers, polyester fibers in brilliant red and purple tones. Their colorations are characterized by excellent fastness properties. Some of the new dyes are also suitable for coloring plastics, which are understood to mean solvent-free and solvent-containing masses made from plastics or synthetic resins.
The process for preparing the sparingly water-soluble azo dyes is that 1 mol of a diazotized amine of the formula
EMI0001.0056
wherein X has the meanings given above, with 1 mol of an azo component of the formula
EMI0001.0059
wherein M, R, s, t and Y have the aforementioned meanings, implements.
The coupling of the diazo compounds with the azo components is preferably carried out in an acidic, optionally buffered, medium. Like the new azo dyes described and produced in the main patent, the dyes listed in the table below can also be produced in a corresponding manner.
They have good drawability and, in some cases, increased nuance purity. The dyes correspond to the formula
EMI0002.0014
EMI0002.0015
<I> table </I>
<tb> Example <SEP> No.
<SEP> X <SEP> y <SEP> s <SEP> t <SEP> u <SEP> w <SEP> Color <SEP> on <SEP> acetate
<tb> 1 <SEP> C-H <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> red
<tb> 2 <SEP> C-H <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH2-OH <SEP> red
<tb> 3 <SEP> C-H <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH3 <SEP> red
<tb> 4 <SEP> C-H <SEP> Cl <SEP> CH3 <SEP> H <SEP> H <SEP> OH <SEP> red
<tb> 5 <SEP> C-H <SEP> Cl <SEP> CH3 <SEP> H <SEP> OH <SEP> <B> CH2 - OH </B> <SEP> red
<tb> 6 <SEP> <B> C <SEP> -H </B> <SEP> Cl <SEP> CH3 <SEP> H <SEP> OH <SEP> CH3 <SEP> red
<tb> 7 <SEP> C-H <SEP> CH3 <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> red-violet
<tb> 8 <SEP> C-H <SEP> CHa <SEP> H <SEP> H <SEP> OH <SEP> <B> CH2 - OH </B> <SEP> red-violet
<tb> 9 <SEP> C-H <SEP> CH3 <SEP> H <SEP> H <SEP> OH <SEP> CH3 <SEP> red-violet
<tb> 10 <SEP> GH <SEP> CH3 <SEP> H <SEP> OH <SEP> H <SEP> OH <SEP> red-violet
<tb> 11 <SEP> C-H
<SEP> CH3 <SEP> H <SEP> OH <SEP> OH <SEP> CH2-OH <SEP> red-violet
<tb> 12 <SEP> GH <SEP> CHs <SEP> H <SEP> OH <SEP> OH <SEP> CH3 <SEP> red-violet
<tb> 13 <SEP> N <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> red
<tb> 14 <SEP> N <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> <B> CH2 - OH </B> <SEP> red
<tb> 15 <SEP> N <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH3 <SEP> red
<tb> 16 <SEP> CJCH3 <SEP> Cl <SEP> H <SEP> H <SEP> H <SEP> OH <SEP> red
<tb> 17 <SEP> C-CH3 <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CH2-OH <SEP> red
<tb> 18 <SEP> C-CH3 <SEP> Cl <SEP> H <SEP> H <SEP> OH <SEP> CHs <SEP> red
<tb> 19 <SEP> C-H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> H <SEP> OH <SEP> red-violet
<tb> 20 <SEP> C-H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OH <SEP> <B> CH2 - OH </B> <SEP> red-violet
<tb> 21 <SEP> C-H <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OH <SEP> CH3 <SEP> red-violet
<tb> 22 <SEP> C-CH3 <SEP> CH3 <SEP> CH3
<SEP> H <SEP> H <SEP> OH <SEP> red-violet
<tb> 23 <SEP> C-CHS <SEP> CH3 <SEP> CH3 <SEP> H <SEP> OH <SEP> CH2-OH <SEP> red-violet
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH807560A CH423036A (en) | 1957-05-29 | 1958-03-15 | Process for the production of azo dyes that are sparingly soluble in water |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4670557A CH370500A (en) | 1957-05-29 | 1957-05-29 | Process for the production of azo dyes that are poorly soluble in water |
| CH4719657A CH418492A (en) | 1957-05-29 | 1957-06-13 | Process for the production of azo dyes that are sparingly soluble in water |
| CH807560A CH423036A (en) | 1957-05-29 | 1958-03-15 | Process for the production of azo dyes that are sparingly soluble in water |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH423036A true CH423036A (en) | 1966-10-31 |
Family
ID=27175923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH807560A CH423036A (en) | 1957-05-29 | 1958-03-15 | Process for the production of azo dyes that are sparingly soluble in water |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH423036A (en) |
-
1958
- 1958-03-15 CH CH807560A patent/CH423036A/en unknown
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